The invention relates to novel substituted N-aryl nitrogen-containing heterocyclic compounds, processes for their preparation and their use as herbicides.
It is known that certain N-aryl nitrogen-containing heterocyclic compounds have herbicidal properties (cf. EP 11693, DE 2952685, DE 3026739, U.S. Pat. Nos. 4,276,420, 4,326,878, WO 94/14817). However, the compounds known from the patent applications mentioned have not acquired noteworthy importance.
The novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I) 
in which
Q1 represents oxygen or sulfur,
Q2 represents oxygen or sulfur,
R1 represents hydrogen, cyano or formyl or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkenyloxy, alkylthio, alkenylthio, alkenylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,
R1 furthermore represents alkenyl or alkinyl, in each case optionally substituted by halogen,
R1 furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
R1 furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl,
R2 represents hydrogen, cyano or formyl, or represents alkyl which is optionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkenylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,
R2 furthermore represents alkenyl or alkinyl, in each case optionally substituted by halogen,
R2 furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each case optionally substituted by halogen,
R2 furthermore represents cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted by halogen, cyano or carboxyl, and
Ar represents the substituted monocyclic or bicyclic aryl or heteroaryl grouping defined below. 
in which
R3 represents hydrogen or halogen,
R4 represents hydrogen or halogen,
R5 represents cyano, carboxyl, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl or halogen, or represents alkyl alkoxy or alkoxycarbonyl, in each case optionally substituted by halogen,
R6 represents the following grouping
xe2x80x94A1xe2x80x94A2xe2x80x94A3
in which
A1 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94COxe2x80x94 or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl alkoxy, aryl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl or arylsulfonyl,
A1 furthermore represents alkanediyl, alkenediyl azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
A2 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A2 furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionally substituted by halogen,
A3 represents hydrogen, with the proviso that in this case A1 and/or A2 do(es) not represent any single bond,
A3 furthermore represents hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl or halogen, or represents alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)-phosphoryl, in each case optionally substituted by halogen or alkoxy,
A3 furthermore represents alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkenylthio, alkinylamino or alkinyloxycarbonyl, in each case optionally substituted by halogen,
A3 furthermore represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, in each case optionally substituted by halogen, cyano, carboxyl, alkyl and/or alkoxy-carbonyl,
A3 furthermore represents aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, in each case optionally substituted by nitro, cyano, carboxyl, halogen, alkyl, halogenalkyl, alkyloxy, halogenalkyloxy and/or alkoxycarbonyl,
A3 furthermore represents in each case optionally completely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy or furylalkoxy, or represents perhydropyranylalkoxy or pyridylalkoxy, and
R7 represents hydrogen or halogen,
or in each case two adjacent radicals xe2x80x94R3 and R4,R4 and R5, R5 and R6 or R6 and R7xe2x80x94together represent one of the following groupings
xe2x80x94Q3xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94Q5xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94Q5xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94Q5xe2x80x94, C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8)xe2x95x90Nxe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94C(R8,R9)xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94N(R10) xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90N(R10)xe2x80x94, xe2x80x94Q3Cxe2x80x94Q4xe2x80x94C(R8,R9)xe2x80x94N(R10)xe2x80x94, Q3xe2x80x94C(R8R9)xe2x80x94(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94
in which
Q3, Q4 and Q5 are identical or different and in each case represent oxygen or sulfur,
R8 and R9 are identical or different and individually represent hydrogen halogen or alkyl or together represent alkanediyl, and
R10 represents hydrogen or hydroxyl, or represents alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl which are optionally substituted by cyano, halogen, alkoxy, alkyl-carbonyl or alkoxy carbonyl, or represents alkenyl or alkinyl, in each case optionally substituted by halogen, or represents cycloalkyl or cycloalkylalkyl, in each case optionally substituted by halogen or alkyl, or represents alkoxy or alkenyloxy, in each case optionally substituted by halogen, or represents arylalkyl or arylalkoxy, in each case optionally substituted by cyano, halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy,
have now been found, the already known compounds 4-(3,4-dichlorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and 4-(4-choro-3-trifluoromethylphenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one (cf DE 2952685 and DE 3026739) being excluded by disclaimer.
The compounds isomeric to the substituted N-aryl nitrogen-containing heterocyclic compounds of the formula (I), of the formulae (Ia) and (Ib) 
in which
Q1, Q2, R1, R2 and Ar have the abovementioned meanings, have furthermore also been found.
The novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I) and, where appropriate, the compounds of the formulae (Ia) or (Ib) are obtained when
(a) (thio)semicarbazide derivatives of the general formula (II) 
in which Ar
Q1, Q2, R1, R2 and Ar have the abovementioned meanings and
R represents alkyl,
are subjected to a cyclizing condensation reaction, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and thereafter, if appropriate, electrophilic or nucleophilic substitution reactions are carried out in the customary manner in the context of the definition of the substituents,
or when
(b) aryliminoheterocyclic compounds of the general formula (III) 
in which
Q1, Q2, R1, R2 and Ar have the abovementioned meanings,
or compounds of the formula (Ia) or (Ib)xe2x80x94abovexe2x80x94
are isomerized themally (xe2x80x9cpyrolyticallyxe2x80x9d), if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
The compounds of the formula (I) can in principle also be synthesized as shown schematically below:
(c) reaction of aryl iso(thio)cyanates of the formula (V) with hydrazines of the formula (V) to give aryl(thio)semicarbazides of the formula (VI) and reaction thereof with (thio)phosgene: 
(d) reaction of aryl iso(thio)cyanates of the formula (V) with S-alkyldithiocarbazates of the formula (VII) and subsequent cyclizing condensation: 
(e) reaction of N,N-bis-chlorocarbonyl- or N,N-bis-phenoxycarbonyl-arylamines of the formula (VIII)xe2x80x94Y:Cl or OC6H5xe2x80x94with hydrazines of the formula (V): 
(f) reaction of arylamines of the formula (IX) with hydrazinedicarboxylic acid esters of the formula (X): 
The compounds of the general formula (I) can also be converted into other compounds of the general formula (I) according to the above definition by further customary methods, for example by customary conversions of carboxlic acid groupings or derivatives thereof (for example R5:COOHxe2x86x92COCl, COOHxe2x86x92COOCH3, COClxe2x86x92CONH2, COOCH3xe2x86x92CONH2CONH2xe2x86x92CN, CNxe2x86x92CSNH2), by alkylation reactions (for example R1: Hxe2x86x92CH3 or CHF2) or by oxidation or sulfurization (for example Q1: Oxe2x86x92S or Sxe2x86x92O)xe2x80x94cf. also the preparation examples.
The novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I) are distinguished by a potent herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen in general represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formulae (I), (Ia) and (Ib) in which
Q1 represents oxygen or sulfur,
Q2 represents oxygen or sulfur,
R1 represents hydrogen, cyano or formyl, or represents C1-C6-alkyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkoxy, C3-C4-alkenyloxy, C3-C4-alkinyloxy, C1-C4-alkylthio, C3-C4-alkenylthio, C3-C4-alkenylthio, C1-C4-alkoxy-carbonyl, C3-C4-alkenyloxy-carbonyl or C3-C4-alkinyloxy-carbonyl,
R1 furthermore represents C3-C6-alkenyl or C3-C6-alkinyl, in each case optionally substituted by fluorine or chlorine,
R1 furthermore represents C1-C6-alkyl-carbonyl, C3-C6-alkenyl-carbonyl, C3-C6-alkinyl-carbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxy-carbonyl or C3-C6-alkinyloxycarbonyl, in each case optionally substituted by fluorine or chlorine,
R1 furthermore represents C3-C6-cycloalkyl or C3-C6-cycloalkyl-carbonyl, in each case optionally substituted by fluorine, chlorine, bromine, cyano or carboxyl,
R2 represents hydrogen, cyano or formyl, or represents C1-C6-alkyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkoxy, C3-C4-alkenyloxy, C3-C6-alkinyloxy, C1-C4-alkylthio, C3-C4-alkenylthio, C3-C4-alkenylthio, C1-C4-alkoxy-carbonyl, C3-C4-alkenyloxyonyl or C3-C4-alkinyloxy-carbonyl,
R2 furthermore represents C3-C6-alkenyl or C3-C6-alkinyl, in each case optionally substituted by fluorine or chlorine,
R2 furthermore represents C3-C6-cycloalkyl-carbonyl, C3-C6-alkinyl-carbonyl, C1-C6-alkoxy-carbonyl, C3-C6-alkenyloxy-carbonyl or C3-C6-alkinyl-carbonyl, C1-C6-alkoxy-carbonyl, C3-C6-alkenyloxy-carbonyl or C3-C6-alkinyloxy-carbonyl, in each case optionally substituted by fluorine or chlorine,
R2 furthermore represents C3-C6-cycloalkyl or C3-C6-cycloalkyl-carbonyl, in each case optionally substituted by fluorine, chlorine, bromine, cyano or carboxyl,
Ar represents the substituted monocyclic or bicyclic aryl or heteroaryl grouping defined below 
in which
R3represents hydrogen, fluorine, chlorine or bromine,
R4represents hydrogen, fluorine, chlorine or bromine,
R5 represents cyano, carboxyl, cholorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl, fluorine, chlorine, bromine or represents alkyl, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms and in each case optionally substituted by fluorine and/or chlorine,
R6 represents the following grouping
xe2x80x94A1xe2x80x94A2xe2x80x94A3
in which
A1 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94COxe2x80x94 or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkyl-carbonyl, phenylcarbonyl, C1-C4-alkyl-sulfonyl or phenylsulfonyl,
A1 furthermore represents C1-C6alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene, in each case optionally substituted by fluorine, chlorine or bromine,
A2 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94COxe2x80x94 or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulfonyl or phenylsulfonyl,
A2 furthermore represents C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene, in each case optionally substituted by fluorine, chlorine or bromine,
A3 represents hydrogen, with the proviso that in this case A1 and/or A2 do(es) not represent a single bond,
A3 furthermore represents hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbarmoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine or bromine,
A3 furthermore represents alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups and in each case optionally substituted by fluorine, chlorine or C1-C4-alkoxy,
A3 furthermore represents alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and in each case optionally substituted by fluorine or chlorine,
A3 furthermore represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and where appropriate 1 to 4 carbon atoms in the alkyl groups and in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkyl and/or C1-C4-alkoxy-carbonyl,
A3 furthermore represents phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, in each case optionally substituted by nitro, cyano, carboxyl, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkyloxy, C1-C4-halogenalkyloxy and/or C1-C4-alkoxy-carbonyl,
A3 furthermore represents in each case optionally completely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazolyl-C1-C4-alkyl, thiazolyl-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, and
R7 represents hydrogen, fluorine or chlorine,
or in each case two adjacent radicalsxe2x80x94R3 and R4, R4 and R5, R5 and R6 or R6 and R7xe2x80x94together represent one of the following groupings
xe2x80x94Qxe2x80x94CQ4xe2x80x94,xe2x80x94Q3xe2x80x94CQ4xe2x80x94Q5xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94Q5xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94, Q3xe2x80x94C(R8R9)xe2x80x94Q5xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8)xe2x95x90Nxe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94C(R8,R9)xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94N(R10)xe2x80x94, C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90Nxe2x80x94N(R10)xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94C(R8,R9)xe2x80x94N(R10)xe2x80x94, Q3xe2x80x94C(R8, R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)
in which
Q3, Q4 and Q5 are identical or different and in each case represent oxygen or sulfur,
R8 and R9 are identical or different and individually represent oxygen, fluorine, chlorine, bromine or C1-C4-alkyl or together represent C2-C5-alkanediyl, and
R10 represents hydrogen or hydroxyl, or represents alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl having in each case 1 to 6 carbon atoms in the alkyl groups and in each case optionally substituted by cyano, fluorine, chlorine, C1-C4-alkoxy, C1-C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl,
R10 furthermore represents alkenyl or alkinyl having in each case 2 to 6 carbon atoms and in each case optionally substituted by fluorine, chlorine or bromine,
R10 furthermore represents cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and where appropriate 1 to 3 atoms in the alkyl group and in each case optionally substituted by fluorine, chlorine, bromine or C1-C4-alkyl,
R10 furthermore represents alkoxy or alkenyloxy having in each case up to 6 carbon atoms and in each case optionally substituted by fluorine and/or chlorine, and
R10 furthermore represents beneyl or benzyloxy, in each case optionally substituted by cyano, fluorine, chlorine, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy,
the already known compounds 4-(3,4-dichoro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and 4(4-chloro-3-trifluoromethyl-phenyl)-1,2-diethyl-5-thioxo-1,2,4-triazolidin-3-one (cf. DE 2952685 and DE 3026739) being excluded by disclaimer.
The invention particularly relates to compounds of the formulae (I), (Ia) and (Ib) in which
Q1 represents oxygen or sulfur,
Q2 represents oxygen or sulfur,
R1 represents hydrogen, cyano or formyl, or represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy,
R1 furthermore represents propenyl, butenyl, propinyl or butinyl, in each case optionally substituted by fluorine or chlorine,
R1 furthermore represents acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, in each case optionally substituted by fluorine or chlorine,
R1 furthermore represents cyclopropyl which is optionally substituted by fluorine or chlorine,
R2 represents hydrogen, cyano or formyl, or represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy,
R2 furthermore represents propenyl, butenyl, propinyl or butinyl, in each case optionally substituted by fluorine or chlorine,
R2 furthermore represents acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, in each case optionally substituted by fluorine or chlorine,
R2 furthermore represents cyclopropyl which is optionally substituted by fluorine or chlorine, and
Ar represents the substituted monocyclic or bicyclic aryl or heteroaryl grouping defined below 
in which
R3 represents hydrogen, fluorine or chlorine,
R4 represents hydrogen, fluorine or chlorine,
R5 represents cyano, thiocarbarmoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
R6 represents the following grouping
xe2x80x83xe2x80x94A1xe2x80x94A2xe2x80x94A3
in which
A1 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94COxe2x80x94 or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A1 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2,-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,
A2 represents a single bond, or represents oxygen, sulfur, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94COxe2x80x94 or the grouping xe2x80x94Nxe2x80x94A4xe2x80x94, in which A4 represents oxygen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A2 furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,
A3 represents hydrogen, with the proviso that in this case A1 and/or A2 do(es) not represent a single bond,
A3 furthermore represents hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfur, fluorine, chlorine or bromine,
A3 furthermore represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy,
A3 furthermore represents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, in each case optionally substituted by fluorine or chlorine,
A3 furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclo-butylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxy carbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl,
A3 furthermore represents phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl, in each case optionally substituted by nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxycarbonyl,
A3 furthermore represents in each case optionally completely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolylmethyl, thiazolylmethyl ,pyridinylmethyl, pyridinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,
R7 represents hydrogen, fluorine or chlorine,
or in each case two adjacent radicalsxe2x80x94R3 and R4, R4 and R5, R5 and R6 or R6 and R7xe2x80x94together represent one of the following groupings
xe2x80x94Q3xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94Q5xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94Q5xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94Q5xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94Q3xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94, Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94, xe2x80x94C(R8)xe2x95x90Nxe2x80x94, xe2x80x94Q3xe2x80x94CQ4C(R8,R9)xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94Q3xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94Q3xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90C(R8)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94C(R10)xe2x80x94, xe2x80x94N(R10)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94, xe2x80x94C(R8)xe2x95x90Nxe2x80x94N(R10)xe2x80x94, xe2x80x94Q3xe2x80x94CQ4xe2x80x94C(R8,R9)xe2x80x94N(R10)xe2x80x94, Q3xe2x80x94C(R8,R9)xe2x80x94C(R8,R9)xe2x80x94CQ4xe2x80x94N(R10)xe2x80x94,
in which
Q3, Q4 and Q5 are identical or different and in each case represent oxygen or sulfur,
R8 and R9 are identical or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl, or together represent ethane-1,2-diyl (dimethylene), and
R10 represents hydrogen or hydroxyl, or represents methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl which are optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl,
R10 furthermore represents propenyl, butenyl, propinyl or butinyl, in each case optionally substituted by fluorine, chlorine or bromine,
R10 furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally substituted by fluorine, chlorine, bromine, methyl or ethyl,
R10 furthermore represents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, in each case optionally substituted by fluorine and/or chlorine, and
R10 furthermore represents benzyl or benzyloxy, in each case optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethyl or trifluoromethoxy,
the already known compounds 4-(3,4-dichloro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and4-chloro-3-trifluoromethyl-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one (cf. DE 2952685 and DE 3026739) being excluded by disclaimer.
The abovementioned definitions of radicals given generally or in preferred ranges apply both to the end products of the formula (I) and also correspondingly to the starting substances or intermediate products in each case required for the preparation. These definitions of radicals can be combined with one another as desired, that is to say also between the stated ranges of preferred compounds.
Examples of the compounds of the formula (I) according to the invention are given in the following groups. 
Ar here has, for example, the meanings listed below:
2,4-dichloro-phenyl, 3-chloro-4-fluoro-phenyl, 2-chloro-4-cyano-phenyl, 2-fluoro-4-cyano-phenyl, 4,5-difluoro-phenyl, 2,4,5-trichloro-phenyl, 2,4-dichloro-5-fluoro-phenyl, 2-chloro-4,5-difluoro-phenyl, 4-chloro-2,5-di-fluoro-phenyl, 5-chloro-2,4-difluoro-phenyl, 2-fluoro-5-chloro-4-cyano-phenyl, 2,4,5-trifluoro-phenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5-fluoro-4-cyano-phenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl, 4-cyano-3-methyl-phenyl, 2-chloro-4-cyano-5-methyl-phenyl, 2,4-dichloro-5-methoxy-phenyl, 2,4dichloro-5-ethoxy-phenyl, 2,4-dichloro-5-n-propoxy-phenyl, 2,4-chloro-5-i-propoxy-phenyl, 4-chloro-2-fluoro-5-methoxy-phenyl, 4-chloro-2-fluoro-5-ethoxy-phenyl, 4-chloro-2-fluoro-5-n-propoxy-phenyl, 4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methyl-phenyl, 2,4-dichloro-5-methyl-phenyl, 2-chloro-4-cyano-5-trifluoromethyl-phenyl, 4-fluoro-3-trifluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl-phenyl, 2-chloro-4-methyl-5-trifluoromethyl-phenyl, 2-chloro-5-fluoro-methoxy-phenyl, 2-fluoro-4-methoxy-5-methyl-phenyl, 2,5-difluoro-4-thicarbamoyl-phenyl, 2-chloro-4fluoro-5-i-propoxy-phenyl 2-fluoro-4cyano-5-methoxy-phenyl, 2-fluoro-4-cyano-5-i-propoxy-phenyl, 2-chloro-4-cyano-5-(2-propinyloxy)-phenyl, 2-fluoro-4-cyano-5-(1-methyl-2-propinyloxy)-phenyl, 2-fluoro-4-chloro-5-(1-methyl-2-propinyloxy)-phenyl, 2-chloro-4-thio-carbamoyl-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-(2-propenyloxy)-phenyl, 2-fluoro-4-chloro-5-(2-propenyloxy)-phenyl,2-chloro-4-cyano-5-methyl-sulfonylamino-phenyl, 2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl, 2-fluoro-4-thiocarbamoyl-5-methylsulfonylamino-phenyl, 2-chloro-4-cyano-5ethylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-cyclopropylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-i-propylsulfonylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-ethylsulfonylamino-phenyl, 2-chloro-4-cyano-5-cyanamino-phenyl, 2-fluoro-4-cyano-5-(2,2-difluoroethylsulfonylamino)-phenyl, 2-fluoro-4-cyano-5-phenyl-sulfonylamino-phenyl, 2-fluoro-4-cyano-5-t-butylsulfonylamino-phenyl, 2-chloro-4-cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl, 2-fluoro-4-chloro-5-ethoxycarbonyl-phenyl, 2-fluoro-4-thiocarbamoyl-5-methoxy-carbonyl-phenyl, 2-chloro-4-cyano-5-(N-cyclopropyl-ethylsulfonylamino)-phenyl, 2-fluoro-4-cyano-5-(1-methyl-2-propinylthio)-phenyl, 2-fluoro-4-cyano-5-methylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-methoxycarbonylmethyl-phenyl, 2-cyano-5-(N-meythyl-ethylsufonylamino)-phenyl, 2-fluoro-4-cyano-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-chloro-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-(bis-ethylsulfonyl-amino)-phenyl, 2-fluoro-4-cyano-5-(N-methylsulfonyl-ethylsulfonylamino)-phenyl, 2-fluoro-4-cyano-5-(1-methoxycarbonyl-ethoxy)-phenyl, 2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethoxy)-phenyl, 2-fluoro-4-chloro-5-(1-methoxycarbonyl-ethoxy)-phenyl, 2-fluoro-4-chloro-5-(1-ethoxycarbonyl-ethoxy)-phenyl, 2-fluoro-4-cyano-5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2-fluoro-4-cyano-5-tetrahydrofurylmethoxy-phenyl, 4-chloro-2-fluoro-5-tetrahydrofurylmethoxy-phenyl, 2-fluoro-4-cyano-5-amino-phenyl, 2-fluoro-4-cyano-5-methylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-methylsulfonyloxy-phenyl, 2-chloro-4-cyano-5-difluoromethoxy-phenyl, 2-fluoro-4-chloro-5-methoxycarbonylmethoxy-phenyl, 2-fluoro-4-chloro-5-ethoxycarbonyl-methoxy-phenyl, 2-fluoro-4-cyano-5-metoxycarbonylmethoxy-phenyl, 2-fluoro-4-cyano-5-ethoxycabonylmethoxy-phenyl, 4-cyano-3-(1-methyl-2-propinyloxy)-phenyl, 2-fluoro-4-cyano-5-dimethylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-cyanomethoxy-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-propenyloxy)-phenyl, 2-fluor-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-nitro-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylamino-phenyl, 2-fluoro-4-cyano-5-chlorosulfonyl-phenyl, 2-fluoro-4-cyano-5-formylamino-phenyl, 2-chloro-4-cyano-5-ethoxycarbonyloxy-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylmethoxy-phenyl, 4-chloro-2-fluoro-5-diethoxy-phosphorylmethoxy-phenyl, 2-fluoro-4-cyano-5-(1-diethoxyphosphoryl-ethoxyphenyl-ethoxy)-phenyl, 2-chloro-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-(N,N-diacetyl-amino)-phenyl, 2-fluoro-4-cyano-5-acetylamino-phenyl, 2-chloro-4-cyano-5-thiocyanato-phenyl, 2-fluoro-4-cyano-5-diethylaminooxy-phenyl, 2-fluoro-4-cyano-5-tetrahydrofuryloxy-phenyl, 2-fluoro-4-cyano-5-ureido-phenyl, 2-fluoro-4-cyano-5-dimethoxymethylenamino-phenyl, 2-chloro-4-cyano-5-ethoxymethylenamino-phenyl, 2-fluoro-4-cyano-5-(2-chloro-ethoxycarbonyl-oxy)-phenyl, 2-chloro-4-cyano-5-dimethylaminomethylenamino-phenyl, 2-chloro-4-cyano-5-(perhydropyran-4-yloxy)-phenyl, 2-fluoro-4-cyano-5-(2-methoxycarbonyl-ethyl)-phenyl, 4-chloro-2-fluoro-5-(2-methoxycarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-5-(2-carboxy-2-chloro-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-bromo-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-bromo-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-bromo-2-ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-bromo-2-ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2,3-dibromo-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2,3-dibromo-2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2,3-dibromo-2-ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-s-butoxycarbonyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-carbamoyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-methoxycarbonyl-1-methyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(1,2-dibromo-2-methoxycarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-5-(2-chloro-2-i-propoxy-carbonyl-ethyl)-phenyl, 2,4-dichloro-5-(2-methoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-carboxy-2-chloro-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-ethylamino-carbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-allylaminocarbonyl-2-chloro-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-methoxycarbonyl-ethenyl)-phenyl, 2-fluoro-4-chloro-5-(2-methoxycarbonyl-ethenyl)-phenyl, 2-fluoro-4-cyano-5-(2-ethoxycarbonyl-ethenyl)-phenyl, 2-fluoro-4-chloro-5-(2-ethoxycarbonyl-ethenyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-methylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-ethylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-cyclopropylamino-carbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-chloro-2-methylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-chloro-2-ethylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-chloro-2-cyclopropylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-dimethylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-ethylsulfonylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-chloro-2-ethylsulfonylaminocarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(2-carboxy-ethenyl)-phenyl, 2-fluoro-4-thiocarbamoyl-5-(2-ethylaminocarbonyl-ethenyl)-phenyl, 2,6-difluoro-4-cyano-5-i-propoxy-phenyl, 2-chloro-4-cyano-6-fluoro-3-i-propoxy-phenyl, 2-choro-6-fluoro-3-i-propoxy-4-trifluoromethyl-phenyl, 2,6-di-chloro-4-cyano-3-fluoro-phenyl, 2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethyl)-phenyl, 2-chloro-4-cyano-5-(1-ethoxycarbonyl-ethyl)-phenyl,2-chloro-4-cyano-5-carboxy-phenyl,2-fluoro-4-chloro-5-(1-ethoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-chloro-5-(1-i-propoxycarbonyl-ethyl)-phenyl, 2-fluoro-4-cyano-5-i-butoxy-phenyl), 2-chloro-4-cyano-5-i-butoxy-phenyl, 2-chloro-4-cyano-5-(2-methoxyethoxy)-phenyl,2-fluoro-4-chloro-5-(2-methoxy-ethoxy)-phenyl,2-fluoro-4-chloro-5-i-butoxy-phenyl, 4-hydroxy-4-ethoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-hydroxy-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-(2-oxetanyloxy)-phenyl, 2-fluoro-4-cyano-5-(2-oxetanyloxy-carbonylmethoxy)-phenyl, 2-fluoro-4-cyano-5-(2-oxetanyloxy)-phenyl, 2-fluoro-4-cyano-5-(2-chloro-2-propenyloxy)-phenyl, 4-chloro-2-fluoro-5-(2-chloro-2-propenyloxy)-phenyl, 2-fluoro-4-chloro-5-methoxycarbonylmethylthio-phenyl, 2-fluoro-4-chloro-5-ethoxycarbonylmethylthio-phenyl, 2-fluoro-4-cyano-5-methoxycarbonylmethylthio-phenyl, 2-fluoro-4-cyano-5-(1-ethoxycarbonylmethylthio)-phenyl, 2-fluoro-4-chloro-5-(1methoxycarbonyl-ethylthio)-phenyl, 2-fluoro-4-chloro-5-(1-ethoxycabonyl-ethylthio)-phenyl, 2-fluoro-4-cyano-5-(1-methoxycarbonyl-ethylthio)-phenyl, 2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethylthio)-phenyl, 
R here represents, for example, hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, i- or s-butyl, alkyl, propargyl, methoxy, ethoxy, n- or i-propoxy, cyanomethyl, carboxymethyl, methoxymethyl, ethoxymethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1. 
Ar here has, for example, the meanings listed above in Group 1.
If, for example, 4-(4-cyano-2,5-difluoro-phenyl)-1-methoxycarbonylthiosemicarbazide is used as the starting substance, the course of the reaction in process (a) according to the invention can be represented by the following equation: 
If for example, 2-(4-choro-2-fluoro-5-methoxy-phenylimino)-3,4dimethyl-3,4-dihydro-5-oxo-1,3,4thiadiazole is used as the starting substance, the course of the reaction in process (b) according to the invention can be outlined by the following equation: 
Formula (II) provides a general definition of the (thio)semicarbazide derivatives to be used as starting substances in process (a) according to the invention for the preparation of the compounds of the general formula (I). In formula (II), Q1, Q2, R1, R2 and Ar preferably or in particular have those meanings which have already been mentioned above as preferred or as particularly preferred for Q1, Q2, R1, R2 and Ar in connection with the description of the compounds of the formula (I); R preferably represents alkyl having 1-4 carbon atoms, in particular methyl or ethyl.
The starting substances of the formula (H) are known and/or can be prepared by known processes (cf. Synthesis 1982, 159-160; DE 1200824, DE 2952685 and DE 3026739).
The (thio)semicarbazide derivatives of the formula (II) are obtained when
(xcex1) aryl iso(thio)cyanates of the general formula (IV)
xe2x80x83Arxe2x80x94Nxe2x95x90Cxe2x95x90Q1xe2x80x83xe2x80x83(IV)
in which
Ar and Q1 have the abovementioned meanings,
are reacted with carbazates of the general formula (XI)
ROxe2x80x94CQ2xe2x80x94N(R2)xe2x80x94NHxe2x80x94R1xe2x80x83xe2x80x83(XI)
in which
Q2, R1 and R2 have the abovementioned meanings and
R represents alkyl, and preferably represents C1-C6 alkyl, and particularly preferably represents methyl or ethyl,
if appropriate in the presence of a diluent, such as, for example, toluene, at temperatures of between 0xc2x0 C. and 150xc2x0 C. (cf. the preparation examples),
or when
(xcex2) arylamines of the general formula (XII)
Arxe2x80x94NH2xe2x80x83xe2x80x83(XII)
in which
Ar has the abovementioned meaning,
are reacted with (thio)carbonyl-diimidazole of the formula (XIII)
Imxe2x80x94CQ1xe2x80x94Imxe2x80x83xe2x80x83(XIII)
in which
Q1 has the abovementioned meaning and
Im represents imidazolyl,
and with carbazates of the general formula (XI)
ROxe2x80x94CQ2xe2x80x94N(R2)xe2x80x94NHxe2x80x94R1xe2x80x83xe2x80x83(XI)
in which
Q2, R1 and R2 have the abovementioned meanings and
R represents alkyl, and preferably represents C1-C6-Calkyl, and particularly preferably represents methyl or ethyl,
if appropriate in the presence of a reaction auxiliary, such as, for example, potassium hydroxide, and if appropriate in the presence of a diluent, such as, for example, methanol, ethanol and/or water, at temperatures of between 0xc2x0 C. and 100xc2x0 C. can be prepared by known processes (cf DE 4327743, DE 4335438 and DE 4343451).
The carbazates of the formula (VIII) futhermore required as precursors are known organic chemicals.
Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. Possible reaction auxiliaries are all the customary organic or inorganic bases. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogencarbonates, such as, for example, lithium sodium, potassium or calcium hydride, lithium, sodium or potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butylate, sodium or potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate, ammmonium acetate, sodium, potassium, rubidium, cesium, magnesium or calcium carbonate, ammonium carbonate and sodium or potassium hydrogencarbonate, and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl- and 4-methyl-pyridine, 2,4-dimethyl-, 2,6dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane, (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Possible diluents for carrying out process (a) according to the invention are the customary organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, methylene chloride, chloroform or carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl or diethyl ether or diethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile, butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric acid triamide; esters, such as methyl, ethyl, n- or i-propyl or n-, i- or s-butyl acetate; sulfoxides, such as dimethyl sulfoxide; alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl or monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether, and mixtures thereof with water or pure water.
The reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. The process is in general carried out at temperatures of between 0xc2x0 C. and +150xc2x0 C., preferably at temperatures between 10xc2x0 C. and 120xc2x0 C.
Process (a) according to the invention is in general carried out under normal pressure. However, it is also possible to carry out the process under increased or reduced pressurexe2x80x94in general between 0.1 bar and 10 bar.
For carrying out process (a) according to the invention, the staring substances of formula (II) are in general initially introduced into the reaction vessel in a suitable diluent andxe2x80x94if appropriate after addition of a reaction auxiliaryxe2x80x94are stirred at the required temperature until the reaction has ended. Working up can be carried out in the customary manner (cf the preparation examples).
Formula (III) provides a general definition of the aryliminoheterocyclic compounds to be used as starting substances in process (b) according to the invention for the preparation of the compounds of the general formula (I). In formula (III), Q1, Q2, R1, R2 and Ar preferably or in particular have those meanings which have already been mentioned above as preferred or as particularly preferred for Q1, Q2, R1, R2 and Ar in connection with the description of the compounds of the formula (I).
The starting substances of the formula (III) are not yet known from the literature; however, they are the subject of a prior application which has not previously been published (cf. DE 4424787).
The aryliminoheterocyclic compounds of the formula (III) are obtained when aryl(thio)semicarbazides of the general formula (VI) are reacted with reactive carbonic acid derivatives, such as, for example, phosgene or thiophosgene, if appropriate in the presence of diluents, such as, for example, toluene and/or methylene chloride, at temperatures of between 0xc2x0 and 100xc2x0 C.
Formulae (Ia) and (Ib) provide general definitions of the compounds to be used, if appropriate, as starting substances, in process (b) according to the invention for the preparation of the compounds of the general formula (I). In formulae (Ia) and (Ib), Q1, Q2, R1, R2 and Ar preferably or in particular have those meanings which have already been mentioned above as preferred or as particularly preferred for Q1, Q2, R1, R2 and Ar in connection with the description of the compounds of the formula (I).
The compounds of the formula (Ia) or (Ib) are obtained when N-aryl nitrogen-containing heterocyclic compounds of the general formula (I) in which at least one of the groups R1 or R2 represents hydrogen are reacted with alkylating or acylating agents of the formulae (IXa or (IXb)
Xxe2x80x94R1xe2x80x83xe2x80x83(XIVa)
Xxe2x80x94R2xe2x80x83xe2x80x83(XIVb)
in which
R1 and R2 have the abovementioned meanings, with the exception of hydrogen, and
X represents halogenxe2x80x94preferably chlorine, bromine or iodinexe2x80x94or one of the groupings xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94R1 or xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94R2,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary at tempt of between 0xc2x0 C. and 80xc2x0 C. (cf. the preparation examples).
The same diluents and reaction auxiliaries as in process (a) according to the invention are preferably possible here.
If appropriate, process (b) according to the invention is carried out in the presence of a reaction auxiliary. The same reaction auxiliaries as in process (a) according to the invention, but furthermore in addition also alkali metal sulfides, such as, for example, sodium sulfide or potassium sulfide, are possible here.
Process (b) according to the invention is preferably carried out using a diluent The same diluents as in process (a) according to the invention are possible here.
The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. The process is in general carried out at temperatures of between 0xc2x0 C. and +250xc2x0 C., preferably at temperatures of between 20xc2x0 C. and 150xc2x0 C.
Process (b) according to the invention is in general carried out under normal pressure. However, it is also possible to carry out the process under increased or reduced pressurexe2x80x94in general between 0.1 bar and 10 bar.
For carrying out process (b) according to the invention, the stating substances of the formula (III) or of the formulae (Ia) or (Ib)xe2x80x94are in general initially introduced into the reaction vessel in a suitable diluent and are stirred at the required temperature until the reaction has ended. Working up can be carried out in the customary manner.
The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver Centamrea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbit.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactlyoctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.
The compounds of the formula (I) according to the invention are particularly suitable for selectively combating monocotyledon and dicotyledon weeds in monocotyledon cultures both by the pre-emergence and by the post-emergence method.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-eulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrobons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.
As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulfite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizain dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Suitable herbicides for the are known herbicides, for example anilides such as, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichioropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quialofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachor, pretilachlor and propachlor, dinitroanilines such as, for example, oryzalin, pendimethalin and trifiuralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulfonylureas such as, for example, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrzosulfuron-ethyl, thifensulfuron-methyl and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for example, atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfureste, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents for improving soil structure is also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the following examples.